Managing Director, Financial Strategy

Fairstead is seeking a Managing Director, Financial Strategy to serve as the financial and operational hub of its corporate platform — a senior leader who owns financial planning, capital strategy, and the systems infrastructure to support one of the country’s most dynamic affordable housing platforms. Fairstead operates across multiple business lines including property management, development, and technology, and is actively investing in AI and digital transformation to operate smarter and grow faster.

Reporting directly to the CEO, this role sits at the intersection of financial strategy and technology. The right candidate brings deep expertise in corporate finance and FP&A, a genuine command of AI and automation, operational excellence and communication skills to engage cross functionally.

Responsibilities:

Financial Strategy & Planning

• Lead Fairstead’s corporate financial strategy, translating long-range objectives into rigorous financial plans and performance targets across all business lines.
• Implement and scale financial systems, processes, and controls to support a growing national platform and additional stand-alone business lines
• Own annual budgeting, multi-year forecasting, and scenario planning to inform decisions on new business lines, geographic expansion, and organizational investments.
• Maintain a corporate-level financial model supporting real-time strategic decision-making; define and monitor KPIs and financial health metrics.

Reporting & Decision Intelligence

• Build and own Fairstead’s corporate reporting infrastructure, ensuring financial and operational data is accurate, timely, and decision-ready.
• Develop corporate reporting packages that synthesize financial performance, strategic progress, and forward-looking risk into a clear narrative.
• Champion data-driven decision-making; drive a culture of financial accountability by ensuring budget owners understand and can act on their numbers.
• Partner with IT function to ensure technology investments are evaluated with clear business cases and measurable ROI.
• Partner with IT to architect the data and reporting systems that underpin financial visibility — from consolidation tools to dashboard infrastructure.
• Deploy AI-driven analytics and automated reporting to drive financial efficiency and reporting accuracy.

Qualifications:

• 12+ years of progressive financial leadership experience at the platform or enterprise level, with demonstrated ownership of corporate financial planning, multi-year forecasting, and executive-level reporting in a complex, multi-entity organization.
• Strong command of financial systems and reporting infrastructure; hands-on experience selecting and implementing FP&A platforms, BI tools, and/or ERP integrations.
• Meaningful experience with AI and automation applied to financial workflows — not just familiarity, but actual deployment and measurable results.
• Exceptional analytical and communication skills; ability to translate complex financial models into clear, executive-ready insights.
• Strategic mindset with comfort in ambiguity, intellectual curiosity, and the discipline to operate fluently across finance and technology.